Triethylamine → HCID 118020858, compound

HRID 575886Notes

Reaction equation

HRID 575886 reaction equation
[O:1]=[S:2]1(=[O:21])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]1[N:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:9]=1[C:10](O)=[O:11].[NH2:22][C:23]1[C:27]([NH2:28])=[N:26][O:25][N:24]=1.C(N(CC)CC)C.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH2:28][C:27]1[C:23]([NH:22][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:18])[F:19])=[N:16][C:8]=2[CH2:7][N:3]2[CH2:4][CH2:5][CH2:6][S:2]2(=[O:1])=[O:21])=[N:24][O:25][N:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 5376773,4-DiaminofurazanHCID 118021016HCID 118021016, compound

Product 1

HCID 118020858HCID 118020858, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

150 mg (0.46 mmol) of 2-[(1,1-dioxido-1,2-thiazolidin-2-yl)methyl]-6-(trifluoromethyl)nicotinic acid and 46 mg (0.46 mmol) of 3,4-diamino-1,2,5-oxadiazole are dissolved at RT in 10 ml of CH2Cl2, and 0.32 ml (2.31 mmol) of triethylamine, 11 mg (0.09 mmol) of DMAP and 442 mg (0.69 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added. The reaction mixture is stirred at RT for 20 h and then washed twice with 5 ml each time of water. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield: 42 mg (22%).

Workup

  1. washwashed twice with 5 ml each time of water
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography (silica gel, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-f37e3002565140ecad033583b6a23fd9
Source dataset
uspto-grants-2015_05
Patent number
US09035064B2

Reaction notes

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